A strategy for the total synthesis of palau'amine is disclosed. The bias of a bicyclic framework is used as a key feature for the enantioselective synthesis of the highly functionalized hexasubstituted cyclopentane core of the molecule. A synthetic approach centering on a tin-catalyzed aldol and a Pauson-Khand reaction is presented. This pathway yielded a penta-substituted cyclopentane ring with four stereocenters positioned and the requisite functionalities to allow for further progress. Installation of the last stereocenter was investigated on a model substrate.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.36914 |
| Date | January 2001 |
| Creators | Dolaine, Regis. |
| Contributors | Gleason, J. L. (advisor) |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001810450, proquestno: NQ70007, Theses scanned by UMI/ProQuest. |
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